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Chemistry

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Also known as: Codeine sulfate, 3-methylmorphine sulfate salt, Schembl24864, Chembl284671
Molecular Formula
C18H23NO7S
Molecular Weight
397.4  g/mol
InChI Key
REJWPZYIFAQSIK-FFHNEAJVSA-N

Codeine Sulfate
Codeine Sulfate is the sulfate salt form of codeine, a naturally occurring phenanthrene alkaloid and opioid agonist with analgesic, antidiarrheal and antitussive activity. Codeine sulfate mimics the actions of opioids by binding to the opioid receptors at many sites within the central nervous system (CNS). Stimulation of the mu-subtype opioid receptor stimulates the exchange of GTP for GDP on the G-protein complex and subsequently inhibits adenylate cyclase. This results in a decrease in intracellular cAMP and leads to a reduction in the release of neurotransmitters such as substance P, GABA, dopamine, acetylcholine and noradrenaline. The analgesic effect of codeine sulfate is likely due to its metabolite morphine, which induces opening of G-protein-coupled inwardly rectifying potassium (GIRK) channels and blocks the opening of N-type voltage-gated calcium channels, thereby resulting in hyperpolarization and reduced neuronal excitability.
1 2D Structure

Codeine Sulfate

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(4R,4aR,7S,7aR,12bS)-9-methoxy-3-methyl-2,4,4a,7,7a,13-hexahydro-1H-4,12-methanobenzofuro[3,2-e]isoquinolin-7-ol;sulfuric acid
2.1.2 InChI
InChI=1S/C18H21NO3.H2O4S/c1-19-8-7-18-11-4-5-13(20)17(18)22-16-14(21-2)6-3-10(15(16)18)9-12(11)19;1-5(2,3)4/h3-6,11-13,17,20H,7-9H2,1-2H3;(H2,1,2,3,4)/t11-,12+,13-,17-,18-;/m0./s1
2.1.3 InChI Key
REJWPZYIFAQSIK-FFHNEAJVSA-N
2.1.4 Canonical SMILES
CN1CCC23C4C1CC5=C2C(=C(C=C5)OC)OC3C(C=C4)O.OS(=O)(=O)O
2.1.5 Isomeric SMILES
CN1CC[C@]23[C@@H]4[C@H]1CC5=C2C(=C(C=C5)OC)O[C@H]3[C@H](C=C4)O.OS(=O)(=O)O
2.2 Synonyms
2.2.1 Depositor-Supplied Synonyms

1. Codeine Sulfate

2. 3-methylmorphine Sulfate Salt

3. Schembl24864

4. Chembl284671

2.3 Create Date
2006-03-21
3 Chemical and Physical Properties
Molecular Weight 397.4 g/mol
Molecular Formula C18H23NO7S
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count8
Rotatable Bond Count1
Exact Mass397.11952325 g/mol
Monoisotopic Mass397.11952325 g/mol
Topological Polar Surface Area125 Ų
Heavy Atom Count27
Formal Charge0
Complexity590
Isotope Atom Count0
Defined Atom Stereocenter Count5
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count2
4 Drug and Medication Information
4.1 Drug Information
1 of 2  
Drug NameCodeine sulfate
Active IngredientCodeine sulfate
Dosage FormTablet; Solution
RouteOral
Strength30mg/5ml; 60mg; 30mg; 15mg
Market StatusPrescription
CompanyLannett Holdings; Roxane

2 of 2  
Drug NameCodeine sulfate
Active IngredientCodeine sulfate
Dosage FormTablet; Solution
RouteOral
Strength30mg/5ml; 60mg; 30mg; 15mg
Market StatusPrescription
CompanyLannett Holdings; Roxane

5 Pharmacology and Biochemistry
5.1 FDA Pharmacological Classification
5.1.1 Pharmacological Classes
Opioid Agonist [EPC]; Full Opioid Agonists [MoA]

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DOSAGE - TABLET;ORAL - 15MG

USFDA APPLICATION NUMBER - 22402

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DOSAGE - TABLET;ORAL - 30MG

USFDA APPLICATION NUMBER - 22402

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DOSAGE - TABLET;ORAL - 60MG

USFDA APPLICATION NUMBER - 22402

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